Benzannulation for the Regiodefined Synthesis of 2-Alkyl/Aryl-1-naphthols: Total Synthesis of Arnottin I

Mal, Dipakranjan; Jana, Amit Kumar; Mitra, Prithiba; Ghosh, Ketaki

doi:10.1021/jo2003677

Cited by 57 publications

(18 citation statements)

References 76 publications

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“…138 Growing interest of benzo [c]coumarin derivatives is dictated mostly by their wide spectrum of biological activity. 146 Naturally occurring compounds which possess analogous structure of 6Hdibenzo[d]naphtho [1,2-b]pyran-6-one, such as Gilvocarcin 147 162 and Arnottin [148][149][150] 163 display biological action such as antibacterial and antitumor. 18).…”

Section: Bio-active Materialsmentioning

confidence: 99%

π-Expanded coumarins: synthesis, optical properties and applications

et al. 2015

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Coumarins fused with other aromatic units have recently emerged as a hot topic of research. Their synthesis is partly based on classical methodologies such as Pechmann reaction or Knoevenagel condensation, but it also sparked the discovery of completely new pathways. In very recent years so-called vertically-expanded coumarins were synthesized, effectively expanding the portfolio of existing architectures. A subtle relationship exists between the structure of fused coumarins and their optical properties. Although absorption of UV-radiation and light is unifying theme among these π-expanded coumarins, the fluorescence properties strongly depend on the structure. The mode of fusion, the type of additional ring and the presence of electron-donating and electron-withdrawing substituents all influence the photophysical parameters. Recent advances made it possible to modulate their absorption from 300 nm to 550 nm, resulting in new coumarins emitting orange light. This review serves as a guide through both synthesis strategies and structure-property relationship nuances. Strong intramolecular charge-transfer character made it possible to reach suitable values of two-photon absorption crosssection. Photophysical advantages of π-expanded coumarins have been already utilized in fluorescence probes and two-photon excited fluorescence microscopy.

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Section: Bio-active Materialsmentioning

confidence: 99%

π-Expanded coumarins: synthesis, optical properties and applications

et al. 2015

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“…The annulation reaction of readily available phthalides 117 with α‐alkyl/arylacrylates 118 for the regiodefined synthesis of alkyl/aryl‐1‐naphthols 119 in the presence of LDA or LHMDS was reported by Mal et al. in 2011 (Scheme ) . This study provided a key intermediate in the synthesis of arnottin I, which is closely related to chelerythrine alkaloids and structurally resembles the anti‐cancer chemical neo‐tanshinlactone.…”

Section: Lda‐ or Lhmds‐mediated Benzannulation Reactionsmentioning

confidence: 77%

Recent Progress in Transition‐Metal‐Free, Base‐Mediated Benzannulation Reactions for the Synthesis of a Diverse Range of Aromatic and Heteroaromatic Compounds

et al. 2018

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Benzene and itsderivativesare the most abundant substructures of several interesting classes of compound, such as bioactive molecules. Owing to their importance, the development of methods for their constructionh as attracted considerable attention.H owever,t he regioselectives ynthesis of polysubstituted aromatic and heteroaromatic compounds by using aromatic substitution is challenging, because it provides derivatives with restricted substitution patterns. Therefore, the benzannulation reaction-the assembly of benzene derivatives from acyclicp recursors-constitutes as uperior and highly versatile approach to polysubstituted aromatic and heteroaromatic compounds,a nd variouse fficient benzannulation reactions have been reported.R epresentative examples include Cs 2 CO 3 , t-BuOK,a nd DBU-catalyzed reactions for the construction of valuableb enzene derivatives. The central objective of this Focus Review is to highlight base-mediated benzannulation reactions under transitionmetal-free conditions for the construction of aromatic and heteroaromatic compounds.[a] Dr.Recently,P an and co-workers investigated the K 2 CO 3 -catalyzed cascade benzannulation reaction of b-keto sulfones 1 with acetylene ketones 2 by using 30 %m ol K 2 CO 3 without other additives,w hich afforded new sulfonylbenzene derivatives 3 in good yields through ab enzannulation reaction (Scheme 1a). [18] Av ariety of electron-donating ande lectron-withdrawing groups were well-tolerated under the optimized reaction conditions. The proposed reactionpathway proceeded through se-quentialM ichael addition, intramolecular cyclization, hydrogen abstraction, and dehydration reactions (Scheme 1b).Scheme55. Synthesis of unsymmetrical biaryls from the annulation/aromatizationr eactionsof1 ,4-pentanedienes with nitroalkanes.Scheme56. DBU-promoted [5+ +1] annulation reaction of a-alkenoyl ketene-S,S-acetalswith nitroalkanes.

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“…The homobenzylic alcohols 9 and 10 were synthesized from the common intermediate naphthol 6, which is itself readily available from 1-naphthol (5) in two steps by allylation [11] followed by Claisen rearrangement at 180°C. [12] Naphthol 6 was protected as either tert-butyldimethylsilyl (TBS) ether 7 by using sodium hydride and TBSCl in 99 % yield [13] or as methyl ether 8 by using dimethyl sulfate and potassium carbonate in 97 % yield. [14] The Wacker oxidation of both 7 and 8 followed by reduction gave homobenzylic alcohols 9 and 10.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of 7‐Deoxy Analogues of the Human Rhinovirus 3C Protease Inhibitor Thysanone

et al. 2013

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The synthesis of (±)‐7‐deoxythysanone and three analogues has been developed. The key oxa‐Pictet–Spengler reaction enabled the synthesis of the naphthopyran precursor, which could be readily converted to 7‐deoxythysanone and three related analogues. The biological activity of these compounds was also evaluated against HRV 3C protease, the results of which suggest that inhibition of the enzyme requires the presence of the 7‐oxa functionality.

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Benzannulation for the Regiodefined Synthesis of 2-Alkyl/Aryl-1-naphthols: Total Synthesis of Arnottin I

Cited by 57 publications

References 76 publications

π-Expanded coumarins: synthesis, optical properties and applications

π-Expanded coumarins: synthesis, optical properties and applications

Recent Progress in Transition‐Metal‐Free, Base‐Mediated Benzannulation Reactions for the Synthesis of a Diverse Range of Aromatic and Heteroaromatic Compounds

Synthesis and Biological Evaluation of 7‐Deoxy Analogues of the Human Rhinovirus 3C Protease Inhibitor Thysanone

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